Isopropyl iodide → HCID 86723696, compound

HRID 577465Notes

Reaction equation

HRID 577465 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:12]([O-])([O-])=O.[K+].[K+].I[CH:19]([CH3:21])[CH3:20].CCO[C:25]([CH3:27])=O>CN(C=O)C>[CH3:11][C:3]1[C:2]([O:1][CH:25]([CH3:27])[CH3:12])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH:19]([CH3:21])[CH3:20])=[O:6]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 86723696HCID 86723696, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-2-methylbenzoic acid (6.00 g, 40.0 mmol) in DMF (40 mL) was added K2CO3 (11.4 g, 82.8 mmol) and 2-iodopropane (8.28 g, 82.8 mmol). The reaction mixture was stirred at room temperature overnight, then heated at 70° C. for 3 hours. The reaction mixture was diluted with EtOAc then filtered through CELITE®. The filtrate was washed with water and brine, dried with Na2SO4, decanted and concentrated under vacuum. The residue was purified by column chromatography (0-30%, EtOAc/heptane) to give propan-2-yl 2-methyl-3-(propan-2-yloxy)benzoate (Cpd MM, 4.0 g, 40%) as a colorless oil.

Workup

  1. temperatureheated at 70° C. for 3 hours
  2. filtrationthen filtered through CELITE®
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customdecanted
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (0-30%, EtOAc/heptane)

Sources & evidence

ORD record
ord-29f67bb50d4c4732b0ce5c67b1b43c44
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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